CN104837824A - Specific polyphenol used in food and drink products, supplements, pharmaceuticals, and the like and method for manufacturing the specific polyphenol - Google Patents
Specific polyphenol used in food and drink products, supplements, pharmaceuticals, and the like and method for manufacturing the specific polyphenol Download PDFInfo
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- CN104837824A CN104837824A CN201380063561.XA CN201380063561A CN104837824A CN 104837824 A CN104837824 A CN 104837824A CN 201380063561 A CN201380063561 A CN 201380063561A CN 104837824 A CN104837824 A CN 104837824A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- General Chemical & Material Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
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- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Pyrane Compounds (AREA)
Abstract
The present invention addresses the problem of providing a method for manufacturing a comparatively high-purity >=4-mer polyphenol by precisely isolating said >=4-mer polyphenol from a polyphenol mixture. This method for manufacturing a specific polyphenol uses a non-acid-containing eluent to isolate a >=4-mer polyphenol from a polyphenol mixture via gel filtration fractionation, e.g. liquid chromatography or gel filtration chromatography.
Description
Technical field
The present invention relates to useful specific polyphenol and manufacture method thereof in diet product, tonic and pharmaceuticals etc.
Background technology
People say, " polyphenol has the effect suppressing to be considered to the active oxygen of the reason of various disease such as cancer, arteriosclerosis ", " polyphenol has the effect etc. suppressing irritated effect and release the pressure ".Therefore, the plant containing polyphenol and the machining object of this plant and extract etc. are widely used in the fields such as diet product, tonic and pharmaceuticals as raw material and additive etc.Particularly, compared with other plant, containing abundant polyphenol in cocoa.Therefore, as such raw material, additive, cocoa powder, cocoa extract etc. are noticeable especially.
As the polyphenol (hereinafter referred to as " cocoa polyphenols ") being derived from cocoa, such as, can enumerate catechin, dimeric procyanidin B 2, trimerical PC1, tetrameric cassia bark tannin A2 etc.
, all the time, can produce the polyphenol of above-mentioned various effect to live body, in cocoa polyphenols, being considered to can be the polyphenol component of less than 3 (i.e. monomer, dimer and tripolymers) by the polymerization degree of intestinal absorption.Just because of this, past has people to propose " being separated the method for (±)-catechin, (±)-l-Epicatechol and their pycnogenols (comprising dimer, tripolymer) from cocoa polyphenols " (such as, Japan's public table No. 2009-501161, Application Publication etc.), someone proposes " method from cocoa polyphenols extraction and isolation ' catechin, l-Epicatechol and their pycnogenols ' or ' senior pycnogenols ' " (such as, the public table of Japan No. 2003-535111, Application Publication).
Prior art document
Patent documentation
Patent documentation 1: Japan public table Application Publication 2009-501161 publication
Patent documentation 2: Japan public table Application Publication 2003-535111 publication
Summary of the invention
The problem that invention will solve
But the polyphenol in recent years more than clear and definite tetramer also has useful effect, effect or purposes.
So, the object of the present invention is to provide a kind of polyphenol being accurately separated more than the tetramer from polyphenol mixture to the method for the polyphenol more than tetramer manufacturing higher degree.
The means of dealing with problems
A first aspect of the present invention relates to the manufacture method of specific polyphenol, and described method uses not containing the elutriant (hereinafter referred to as " not containing sour elutriant ") of acid, is separated the polyphenol of more than the tetramer from polyphenol mixture gel-filtration.In addition, " polyphenol " mentioned here refers to the general name of the plant constituent with multiple phenolic hydroxyl group.Further, " polyphenol mixture " mentioned here is such as cocoa extract.And then, the pycnogenols more than preferred tetramer of the polyphenol (hereinafter referred to as " specific polyphenol ") more than tetramer.In addition, " pycnogenols " refers to the oligomer of the catechin such as catechin, l-Epicatechol.Further, the upper limit of the polymerization degree of polyphenol or pycnogenols preferably 20.In addition, gel-filtration is separated and such as can uses liquid chromatography (comprising high performance liquid chromatography), gel filtration chromatography.In addition, now as gel filtration material, Chemical bond is preferably used to have the silica gel particle of glycerine propyl group (グ リ セ ロ プ ロ ピ Le base).
In addition, in the manufacture method of this specific polyphenol, gel-filtration is separated and preferably makes not changing containing the composition of sour elutriant as elutriant.Further, preferably make the composition not containing sour elutriant that the change of at least four-stage occurs.Effectively can suppress the polyphenol being mixed into below tripolymer in this specific polyphenol.
The result that the present application person further investigate shows, utilizes the manufacture method of this specific polyphenol, is accurately separated the polyphenol of more than the tetramer from polyphenol mixture, can manufacture the polyphenol of more than the tetramer of higher degree.Now, this specific polyphenol is not preferably containing the pycnogenols below catechin, l-Epicatechol and tripolymer.But, this means " in fact " not containing the pycnogenols below catechin, l-Epicatechol and tripolymer.In a word, alternatively, this specific polyphenol is following polyphenol mixture: " total mass of the polyphenol more than tetramer " relative to the ratio of " total mass of the polyphenol below catechin, l-Epicatechol and tripolymer " be more than 9, preferably more than 10, more preferably more than 11, more preferably more than 12.In addition, the upper limit of this ratio is infinitely great (∞), and this ratio is more high better, but such as, the upper limit of this ratio is 100.
A second aspect of the present invention relates to specific polyphenol, and in described specific polyphenol, the polyphenol content below tripolymer is at below 10 quality %.In addition, the polyphenol content below preferred tripolymer is at below 9 quality %, more preferably below 8 quality %, more preferably below 7 quality %, particularly preferably below 6 quality %, most preferably below 5 quality %.
Now, as polyphenol, such as, if use cocoa polyphenols, from the view point of its security and local flavor, physical property etc., specific polyphenol preferably as diet product raw material (material, composition), tonic raw material (material, composition) and pharmaceuticals raw material (material, composition) etc., more preferably as diet product raw material and tonic raw material, more preferably as diet product raw material.
Accompanying drawing explanation
Fig. 1 represents the result figure that the gel-filtration of embodiment 1 is separated.
Fig. 2 represents the result figure that the gel-filtration of embodiment 2 is separated.
Fig. 3 represents that the gel-filtration of embodiment 2 is separated the analytical results figure of the content of the high-polymerization degree pycnogenols contained in rear each component, [a) cocoa extract (CLPr), b) oligomeric component (CLPr-L), c) high poly-component (CLPr-H)].
Fig. 4 represents the result figure that the gel-filtration of comparative example 1 is separated.
Embodiment
The cocoa procyanidins (hereinafter referred to as " high poly-pycnogenols ") more than tetramer of embodiment of the present invention can be obtained through gel-filtration separation by cocoa extract.In addition, this gel-filtration is separated and uses " not containing the elutriant of acid " as elutriant.In addition, cocoa extract also can to buy on market product sold etc., also can be extracted from cocoa beans, cocoa powder by known method." cocoa beans " that may be used for embodiment of the present invention by the place of production, upgrowth situation, with or without restrictions such as roastings.
Gel-filtration is separated can use the known means such as high performance liquid chromatography (HPLC), gel filtration chromatography (GFC).In addition, from the viewpoint of the easness operated on a laboratory scale and reproducibility etc., preferred use HPLC, in the scope obtaining the equal separation efficiency with laboratory scale, also can be enlarged into pilot scale (パ イ ロ ッ ト プ ラ Application ト Regulations mould) and commercial production scale (Actual Machine Regulations mould).In this case, as a kind of embodiment of gel filtration material, preferred use positive separatory " Chemical bond has the silica gel particle of glycerine propyl group ", the molecule utilizing polarity low by wash-out (in the present invention first, in order by wash-out the polyphenol low by the polymerization degree) principle, implement HPLC, GFC etc.
" not containing the elutriant of acid " mentioned here is meant in fact not containing the elutriant of the acetic acid, phosphoric acid, formic acid, trifluoroacetic acid etc. that usually add in elutriant.In addition, in embodiments of the present invention, as such elutriant, applicable use is acetonitrile, methyl alcohol polar organic solvent, water or their mixing solutions such as.In addition, " containing acid " can be separated into benchmark by the gel-filtration of the cocoa polyphenols (cocoa procyanidins) not affecting in fact more than the cocoa polyphenols of below tripolymer and the tetramer and judge.
Embodiment
Next, by embodiment, the present invention will be described in more detail.But the present invention is not limited only to following examples.In addition, following term " oligomeric " refer to the polymerization degree more than 1, the meaning of less than 3 (i.e. monomer ~ tripolymers), term " high poly-" refers to polymerization degree meaning of (namely more than the tetramer) more than 4.
Embodiment 1
(1) preparation of material solution
The cocoa extract (hereinafter referred to as " CLPr ") that Ecuador originates in is dissolved in methanol aqueous solution (50 quality %), makes the concentration of CLPr be 30mg/ml.Then, this CLPr solution is used the regenerated cellulose membrane filtration in 0.45 μm, aperture, raw materials solution.
(2) gel-filtration is separated
The envrionment conditions of high performance liquid chromatography (hereinafter referred to as " HPLC ") system is set according to shown below.Then, material solution above-mentioned for 50 μ l is injected HPLC system, using the elution fraction of 8 minutes to 16 minutes after material solution injection as oligomeric component (hereinafter referred to as " CLPr-L "), the elution fraction of 17 minutes to 25 minutes after material solution injects is gathered component (hereinafter referred to as " CLPr-H ") as height, respective separated and collected (with reference to Fig. 1).As shown in Figure 1, in the present embodiment, tripolymer is separated completely with tetrameric peak.Therefore, in CLPr-L, mainly containing catechin, l-Epicatechol and their dimer and tripolymer; In CLPr-H, main containing the pycnogenols more than tetramer.That is, the content containing high poly-pycnogenols in each component, the yield of each component and coming to the same thing of following embodiment 2.In addition, as this separation point, be set as the time point of CLPr-H as much as possible containing catechin, l-Epicatechol and their dimer and trimerical pycnogenols.
(envrionment conditions of HPLC system)
Device: semi-preparative liquid chromatography system (Japanese Shimadzu society manufactures, System's composition: 2 LC-6AD, CBM-20A, CTO-20A, SIL-10AF, SPD-20A, FRC-10A, LCsolution softwares)
Post: Deverosil 100Diol-58.0 × 300mm
Flow velocity: 2.4ml/ minute
Determined wavelength: UV 280nm
Elutriant: the methanol aqueous solution of acetonitrile and 97 quality %
Gradient: (the quality % of the methanol aqueous solution of 97 quality %) 0 (0 minute), 20 (4 ~ 9 minutes), 40 (13 ~ 18 minutes), 0 (20 ~ 30 minutes)
Embodiment 2
(1) preparation of material solution
Similarly to Example 1, CLPr is prepared.
(2) gel-filtration is separated
The envrionment conditions of HPLC system is changed according to shown below: 1960 μ l above-mentioned raw materials solution are injected this HPLC system.Then, using the elution fraction of 45 minutes to 85 minutes after material solution injection as CLPr-L, using the elution fraction of 90 minutes to 135 minutes after material solution injection as CLPr-H, in addition, similarly to Example 1, respective separated and collected (with reference to Fig. 2).
(envrionment conditions of HPLC system)
Device: a large amount of preparation liquid chromatographic system (Japanese Shimadzu society manufactures, System's composition: 2 LC-8A, FCV-130AL, SIL-10AP, SPD-20AV, FRC-10A, LC solution softwares)
Guard column: Deverosil 100Diol-10 50 × 100mm
Principal post: Deverosil 100Diol-10 50 × 300mm
Flow velocity: 20.8ml/ minute
Determined wavelength: UV 280nm
Elutriant: the methanol aqueous solution of acetonitrile and 97 quality %
Gradient: (the quality % of the methanol aqueous solution of 97 quality %) 0 (0 minute), 20 (24 ~ 54 minutes), 40 (78 ~ 108 minutes), 0 (120 ~ 180 minutes)
(3) height contained in each component gathers the content analysis of pycnogenols
Each elution fraction of above-mentioned CLPr-L and CLPr-H is respectively collected 2 ~ 4ml, respective dry solidification in centrifugal evaporator.Then, use the methanol aqueous solution (50 quality %) of 100 μ l, each elution fraction of this drying is dissolved, separately again as sample.
Method according to Kelm etc. use pycnogenols class positive HPLC assay method (with reference to people such as Kelm, M.A., J.Agric Food Chem 2006,54 (5); P.1571 ~ 1576), with l-Epicatechol equivalent, above-mentioned each sample is analyzed, obtain the result shown in the analysis chart shown in Fig. 3 and table 1.
Table 1
Containing more than the pycnogenols 90 quality % more than tetramer in CLPr-H.On the other hand, the pycnogenols of more than the tetramer is not detected in CLPr-L.In addition, for these pycnogenolss, with analysed by reverse phase HPLC method for benchmark, be made typical curve with l-Epicatechol, the procyanidin concentration of each polymerization degree be scaled l-Epicatechol equivalent and carry out quantitatively.
(4) yield of each component
Each elution fraction of above-mentioned CLPr-L and CLPr-H is in evaporator for decompression, and removing organic solvent concentrates.Then, the elution fraction this be concentrated is transferred to metal vessel ,-80 DEG C of freeze-drying while using ultrapure water cleaning.Then, weigh the weight of each elution fraction, obtain CLPr-L and CLPr-H yield separately, the yield of CLPr-L is the yield of 33%, CLPr-H is 40%.Comparative example 1
(1) preparation of material solution
Similarly to Example 1, CLPr is prepared.
(2) gel-filtration is separated
The envrionment conditions of HPLC system is changed according to shown below: 50 μ l above-mentioned raw materials solution are injected this HPLC system.Then, using the elution fraction of 8 minutes to 18.5 minutes after material solution injection as CLPr-L, using the elution fraction of 19 minutes to 30 minutes after material solution injection as CLPr-H, in addition, similarly to Example 1, respective separated and collected (with reference to Fig. 4).As shown in Figure 4, in this comparative example, tripolymer and tetrameric peak close.Therefore, relatively largely containing catechin, l-Epicatechol and their dimer and trimerical pycnogenols in CLPr-H, the CLPr-H obtaining higher degree is difficult to.
(envrionment conditions of HPLC system)
Device: semi-preparative liquid chromatography system (Japanese Shimadzu society manufactures, System's composition: 2 LC-6AD, CBM-20A, CTO-20A, SIL-10AF, SPD-20A, FRC-10A, LCsolution softwares)
Post: Deverosil 100Diol-58.0 × 300mm
Flow velocity: 2.4ml/ minute
Determined wavelength: UV 280nm
Elutriant: the acetonitrile solution (2 quality %) of acetic acid and the acetate-methanol aqueous solution (acetic acid: 2 quality %, methyl alcohol: 95 quality %)
Gradient: (the quality % of the acetate-methanol aqueous solution) 0 (0 minute), 40 (18 ~ 23 minutes), 0 (25 ~ 35 minutes)
From the research of the result of embodiment and comparative example
" representing Fig. 1 and Fig. 2 of the gel-filtration separating resulting of embodiment 1 and embodiment 2 " is contrasted known with " representing Fig. 4 of the gel-filtration separating resulting of comparative example 1 ", in the former, the trimerical timed interval detecting peak the latter compared with the tetrameric timed interval detecting peak is longer.Therefore, can think, compared with the past, embodiment 1 is separated with embodiment 2 and obtains more highly purified height and gather pycnogenols (that is, the pycnogenols more than the tetramer).Usually, in order to be separated polyphenol more accurately from polyphenol crude extract, generally in gel-filtration separation eluent, add acid.To this, in the gel-filtration separation method of the present embodiment, expressly do not add acid, can make thus trimerically to detect peak and the tetrameric timed interval detecting peak broadens.So its result can obtain highly purified height and gather pycnogenols.
Industrial applicibility
In the manufacture method of specific polyphenol of the present invention, highly purified height can be obtained and gather cocoa procyanidins (that is, the cocoa procyanidins more than the tetramer).In addition, the manufacture method of specific polyphenol of the present invention is not limited to gather pycnogenols from cocoa powder and cocoa extract by gel-filtration separation and Extraction height, also can apply from the other plant containing polyphenol and diet product etc. (such as, tea, fruit (grape, apple, blueberry etc.), cereal (sesame, soybean, buckwheat etc.) or their powder and their extract) by during gel-filtration separation and Extraction polyphenol.
In addition, the height through the manufacture method manufacture of specific polyphenol of the present invention gathers pycnogenols, such as, not only can use as the effective constituent of the pharmaceuticals such as blood glucose value control agent etc., also can make an addition in diet product, tonic etc. and use.In addition, these pharmaceuticals etc. also can oral administration give, and also can give through pipe, also can give through intestines.
Claims (5)
1. the manufacture method of specific polyphenol, wherein, described method uses not containing the elutriant of acid, is separated the polyphenol of more than the tetramer from polyphenol mixture gel-filtration.
2. the manufacture method of specific polyphenol as described in claim 1, wherein, carries out gel-filtration separation while above-mentioned elutriant composition is changed.
3. the manufacture method of specific polyphenol as claimed in claim 1 or 2, wherein, as gel filtration material, uses Chemical bond to have the silica gel particle of glycerine propyl group.
4. use the specific polyphenol containing the polyphenol more than tetramer that the manufacture method of the specific polyphenol as described in any one of claims 1 to 3 manufactures.
5. specific polyphenol, wherein, the polyphenol content below tripolymer is at below 10 quality %.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012273126 | 2012-12-14 | ||
| JP2012-273126 | 2012-12-14 | ||
| PCT/JP2013/083429 WO2014092175A1 (en) | 2012-12-14 | 2013-12-13 | Specific polyphenol used in food and drink products, supplements, pharmaceuticals, and the like and method for manufacturing said specific polyphenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104837824A true CN104837824A (en) | 2015-08-12 |
| CN104837824B CN104837824B (en) | 2017-10-20 |
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| CN201380063561.XA Active CN104837824B (en) | 2012-12-14 | 2013-12-13 | Specific polyphenol and its manufacture method that diet product, tonic and pharmaceuticals etc. are used |
Country Status (4)
| Country | Link |
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| JP (1) | JP6297501B2 (en) |
| CN (1) | CN104837824B (en) |
| HK (1) | HK1207646A1 (en) |
| WO (1) | WO2014092175A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3509891B2 (en) * | 1993-02-24 | 2004-03-22 | サントリー株式会社 | Flavonoid polymer and glucosyltransferase inhibitor containing the same as active ingredient |
| JPH10218769A (en) * | 1997-02-06 | 1998-08-18 | Kikkoman Corp | Antiulcer agent |
| ATE337310T1 (en) * | 1999-04-23 | 2006-09-15 | Kyowa Hakko Kogyo Kk | METHOD FOR PURIFYING PROANTHOCYANIDINE OLIGOMERS |
| JP2005314316A (en) * | 2004-04-30 | 2005-11-10 | Kikkoman Corp | Anti-sars coronavirus agent |
| TW200637542A (en) * | 2004-12-22 | 2006-11-01 | Kikkoman Corp | Lipase inhibitor, preventing and treating agent of skin disease |
| JP5337574B2 (en) * | 2009-05-08 | 2013-11-06 | フジッコ株式会社 | Separation and purification method of proanthocyanidins |
| JP5569716B2 (en) * | 2009-06-23 | 2014-08-13 | 独立行政法人国立循環器病研究センター | Drug for inhibiting lectin-like oxidized LDL receptor |
| JP2011178728A (en) * | 2010-03-02 | 2011-09-15 | Kobe Univ | Ampk activator, glut4 activator and pharmaceutical drug and food and drink using the same |
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2013
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- 2013-12-13 CN CN201380063561.XA patent/CN104837824B/en active Active
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| Publication number | Publication date |
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| WO2014092175A1 (en) | 2014-06-19 |
| CN104837824B (en) | 2017-10-20 |
| JP6297501B2 (en) | 2018-03-20 |
| HK1207646A1 (en) | 2016-02-05 |
| JPWO2014092175A1 (en) | 2017-01-12 |
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